Aniline → Methyl 5-methyl-4-(phenylamino)thiophene-2-carboxylate

Participants

Reaction Steps

A stirred suspension of 400 mg (1.7 mmol) methyl 5-methyl-4-bromo-thiophene-2-carboxylate and 192 μL (2.1 mmol, 1.25 eq) of aniline (Aldrich, Milwaukee, Wis.) was treated in a manner similar to Example 241, step (b) to give 66 mg of the title compound (16%) as a brown glass. 1H-NMR (DMSO-d6, 400 MHz) δ7.70 (s, 1H), 7.56 (s, 1H), 7.17 (m, 2H), 6.72 (m, 3H), 3.79 (s, 3H), 2.31 (s, 3H). Mass spectrum (MALDI, gentisic acid matrix, m/z): Calcd. for C13H13NO2S, 248.1 (M+H), found 247.5.

Provenance & Evidence